On his first day at the penitentiary, in 1994, Raynald Desjardins made a point of shaking the hand of the warden in front of other inmates, assuring him that "all would go well."
Mr. Desjardins, who was serving a 15-year sentence for cocaine trafficking, then proceeded to act as if he ran the place, getting involved in two murder plots and a conspiracy to poison the prison staff.
The incident, which is documented in Mr. Desjardins' parole records, illustrates the cocky, velvet-glove-in-iron-fist style of a man described in court documents as a major Quebec organized-crime figure.
Mr. Desjardins is in the news spotlight this week after a witness at the Charbonneau public inquiry described how the 60-year-old mobster acted as if he controlled FTQ-Construction, one of the province's biggest and richest trade unions.
The witness, Ken Pereira, was a whistleblowing union leader who had been clashing with his boss, FTQ-Construction executive director Jocelyn Dupuis.
Mr. Pereira testified that he was called around 2008 or 2009 to have brunch at a hotel. Ten thuggish-looking men stood at the door. Inside, Mr. Pereira was told that he would meet Mr. Desjardins and that he was to speak politely to him.
Mr. Desjardins showed up and said: "Listen Ken, I don't know if you know me but I did 11 years in jail. I kept my mouth shut, I did my time and that's the way it should be."
Mr. Desjardins said that he could get Mr. Dupuis removed because he didn't want to see more union feuding since "we've got more important business to do."
Mr. Pereira testified that he got scared. "At that moment, I discovered that Jocelyn Dupuis, who I thought was the boss, wasn't the boss. Raynald Desjardins was the boss."
While he is not as famous as the Hells Angel chieftain Maurice (Mom) Boucher, or the Mafia don Vito Rizzuto, court evidence shows that Mr. Desjardins is an influential kingpin who once had almost daily contacts with Mr. Rizzuto and Mr. Boucher.
Mr. Desjardins is a former confidant of Mr. Rizzuto and is a rare francophone Quebecker allowed in the inner circles of Montreal's Sicilian mob, the Charbonneau inquiry has heard.
However, Mr. Desjardins could never become a full-fledged "made man" because he is not of Italian ancestry, RCMP Corporal Linda Féquière told the inquiry.
"Since you were young you've moved up in the world of the Sicilian Mafia. You adopted their values, espoused their way of life and practised their criminal activities to fulfill your needs for power, recognition and feeling accepted," the parole board said in a 2000 decision about him.
Mr. Desjardins has been back in custody since December 2011 after he was charged with first-degree murder following the shooting death of Salvatore (Sal the Ironworker) Montagna, identified by the FBI as a former head of the Bonanno crime family of New York.
At the time of his killing, Mr. Montagna was believed to have been trying to take over Montreal's underworld in the absence of Mr. Rizzuto, who was serving a sentence in the U.S.
Mr. Desjardins appeared to have been in the middle of that power struggle. Three months before his arrest, he survived an assassination attempt when a motorist fired at him while he was in his SUV.
By last year, Mr. Rizzuto had finished serving his prison term in the U.S. and was back in Canada. Within a month, Mr. Desjardins' brother-in-law, the mobster Joe Di Maulo, was shot dead in his driveway.
While Mr. Desjardins describes himself as an entrepreneur, he has a criminal record dating back to 1971, when he was 18 and convicted for drug possession.
In 1987, Mr. Desjardins and Mr. Rizzuto were charged with smuggling 16 tonnes of hashish via Newfoundland. The case was dismissed on a technicality after the RCMP was caught trying to illegally wiretap the defence lawyers' restaurant table.
In 1991, Mr. Desjardins and Mr. Rizzuto were linked to another massive drug case. They were named in an investigation into a plot to smuggle 50 tonnes of hashish from Lebanon, according to a Montreal police court affidavit, which said the two men were heard on the phone, using veiled terms and talking in "a friendly and familiar tone."
The authorities eventually caught up with Mr. Desjardins when he was convicted in 1994 for importing 740 kilograms of cocaine from Venezuela.
Sentenced to 15 years, he was identified by the parole board as as a kingpin "who tries to live inside prisons as he has done outside, with underlings and middlemen. They impose their way of life through intimidation and violence."
Parole board commissioners alleged that Mr. Desjardins was known by other inmates as "the millionaire," had control of the prison's fridges and telephones and got himself moved to a row of cells where he could phone out every day and conduct business, contrary to institutional policy.
The parole record also alleges that Mr. Desjardins once asked two inmates to find volunteers to execute a contract killing. He also got a jogging track overhauled, which the parole board saw as "a spectacular way to show your strength and power within the institution."
Mr. Desjardins was repeatedly denied parole, because commissioners felt he didn't show signs he was rehabilitated. "The easy life, the parties, the great restaurants and golf are still big attractions to you."
After finally getting parole in 2004, Mr. Desjardins became the main shareholder of a construction company incorporated under various names, including Desj. & Cie. and investissements Lasister et Kane.
In an interview with La Presse two years ago, Mr. Desjardins acknowledged his past criminal record but said he is now a construction entrepreneur, which, he said, explained his friendship with Mr. Dupuis, the former executive-director of the FTQ-Construction, who is facing charges of fraud, forgery and conspiracy.